The song's music video won many awards. "The Boys of Summer" was also performed live by Henley with the reunited Eagles; such a version is included on the group's 2005 Farewell 1 Tour-Live from Melbourne DVD.

Henley's song is cemented by Campbell's 1-7-5 repetitive riff over a vi-IV-V-IV chord pattern. Superficially, the song appears to be about the passing of youth and entering middle age, with the theme of 'summer love' apparent in the choruses, and of reminiscence of a past relationship.[1]

In an interview with NME in 1985, Henley explained the 'Deadhead sticker on a Cadillac' lyrics as an example of his generation selling out:

"I was driving down the San Diego Freeway and got passed by a $21,000 Cadillac Seville, the status symbol of the Right-wing upper-middle-class American bourgeoisie – all the guys with the blue blazers with the crests and the grey pants – and there was this Grateful Dead 'Deadhead' bumper sticker on it!"[6][7]

In an interview with Knoxville.com, Neil Giraldo, Pat Benatar's guitarist and husband, says that Henley came in the studio while he was in the process of recording the song "Love Is a Battlefield" using an up tempo beat, and asked Giraldo if he could steal the sound for use in his song, "The Boys of Summer", to which Giraldo gave his permission.[8] Both "Love Is A Battlefield" and "The Boys of Summer" rely heavily on the Linn LM-2drum machine.

The music video to "The Boys of Summer" is a French New Wave-influenced piece directed by Jean-Baptiste Mondino. Shot in black-and-white, it shows the main character of the song at three different stages of life (as a young boy, a young adult and middle-aged), in each case reminiscing about the past relationship. This is shown during the line "A little voice inside my head said don't look back, you can never look back" at which point, each of the three people look back in turn. The young boy in the video, played by seven-year-old Josh Paul,[11] resembles a young Don Henley. The girl in the music video is played by Audie England.

Interspersed with these scenes are segments of Henley miming the words of the song while driving in a convertible. At its conclusion, the video uses the post-modern concept of exposing its own workings, as with a wry expression Henley drives the car away from a rear projection screen.

In 2002, Spanish trance artist DJ Sammy (with vocals performed by Loona) covered the song. It was released in November 2002 as the third and last single released from the album Heaven. This cover peaked at number 2 in the United Kingdom. It was certificated Platinum by RIANZ.[24]

In 2003, the rock band the Ataris covered "The Boys of Summer" for their album So Long, Astoria. The song became their second single when a radio station began to play it. The Ataris's version of the song replaced the "Deadhead sticker" reference with one more appropriate to the age group of their fans, namely a "Black Flag sticker", in honor of the punk rock band from the 1980s. The single peaked at No. 2 on the Billboard Modern Rock Chart (held off the No. 1 top spot by Linkin Park's "Faint") and No. 20 on the Billboard Hot 100. It remains their most successful single to date.[38]

^Gilmore, Mikal (November 5 – December 10, 1987). "Henley Interview 1987". Rolling Stone. 512 (20th Anniversary Issue). Archived from the original on 2008-10-10. Retrieved September 9, 2008. Beyond that, I'm also not convinced we really accomplished all that much. Kennedy was president and everybody thought it was Camelot, but look at what we did. We raised all that hell in the Sixties, and then what did we come up with in the Seventies? Nixon and Reagan. The country reverted right back into the hands it was in before. I don't think we changed a damn thing, frankly. That's what the last verse of 'The Boys of Summer' was about. I think our intentions were good, but the way we went about it was ridiculous. We thought we could change things by protesting and making firebombs and growing our hair long and wearing funny clothes. But we didn't follow through. After all our marching and shouting and screaming didn't work, we withdrew and became yuppies and got into the 'Me' Decade.